This invention relates to o-haloalkylbenzene sulfonyl ureas which are useful as herbicides.
Netherlands Pat. No. 121,788, published Sept. 15, 1966, teaches the preparation of compounds of Formula (i), and their use as general or selective herbicides, ##STR1## wherein R.sub.1 and R.sub.2 may independently be alkyl of 1-4 carbon atoms; and
R.sub.3 and R.sub.4 may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms. PA1 R.sub.4 is hydrogen, fluorine, chlorine, bromine or methyl; PA1 R.sub.5 is hydrogen, fluorine, chlorine, bromine methyl or methoxy; PA1 R.sub.7 is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms or alkoxy of 1-2 carbon atoms; PA1 R.sub.8 is hydrogen, methyl, chlorine or bromine; PA1 R.sub.9 and R.sub.10 are independently hydrogen, methyl, chlorine or bromine; PA1 W and Q are independently oxygen or sulfur; PA1 n is 0, 1 or 2; PA1 X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1-3 carbon atoms, trifluoromethyl, CH.sub.3 S-- or CH.sub.3 OCH.sub.2 --; and PA1 Z is methyl or methoxy; PA1 (a) when R.sub.5 is other than hydrogen, at least one of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 is other than hydrogen and at least two of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be hydrogen; PA1 (b) when R.sub.5 is hydrogen and all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 are other than hydrogen, then all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be either chlorine or methyl; and PA1 (c) when R.sub.3 and R.sub.7 both are hydrogen, at least one of R.sub.4, R.sub.5 or R.sub.6 must be hydrogen. PA1 R is H, F, Cl, Br, NO.sub.2, CF.sub.3, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy; PA1 R.sub.1 is H, F, Cl or C.sub.1 -C.sub.4 alkyl; PA1 R.sub.2 is H or CH.sub.3 ; PA1 R.sub.3 is H, C.sub.1 -C.sub.4 alkyl or OCH.sub.3 ; PA1 R.sub.4 is H or C.sub.1 -C.sub.4 alkyl; PA1 R.sub.3 and R.sub.4 can be taken together to form --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --(CH.sub.2).sub.2 O(CH.sub.2).sub.2 --; PA1 R.sub.4 ' is H, CH.sub.3 or CH.sub.2 CH.sub.3 ; PA1 R.sub.5 is C.sub.1 -C.sub.4 alkyl optionally substituted with 1-3 atoms of F, Cl or Br, or C.sub.3 -C.sub.4 alkenyl; PA1 R.sub.6 is H, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.4 alkenyl; PA1 R.sub.7 is C.sub.1 -C.sub.4 alkyl; PA1 R.sub.8 is H, CH.sub.3 or OCH.sub.3 ; PA1 A is ##STR6## W is O or S; X is H, Cl, Br, CH.sub.3, CH.sub.2 CH.sub.3, C.sub.1 -C.sub.3 alkoxy, CF.sub.3, SCH.sub.3 or CH.sub.2 OCH.sub.3 ; PA1 Y is CH.sub.3 or OCH.sub.3 ; PA1 Z is N, CH, CCl, CBr, CCN, CCH.sub.3, CCH.sub.2 CH.sub.3, CCH.sub.2 CH.sub.2 Cl or CCH.sub.2 CH.dbd.CH.sub.2 ; PA1 Y.sup.1 is H, CH.sub.3, OCH.sub.3 or OCH.sub.2 CH.sub.3 ; and PA1 Q is O or CH.sub.2 ; PA1 (1) when R.sub.1 is Cl, then L is Cl or Br and R.sub.2 is H; PA1 (2) when R.sub.3 is OCH.sub.3, then R.sub.4 is CH.sub.3 ; PA1 (3) when W is S, then R.sub.8 is H; and PA1 (4) when L is F, then R.sub.1 is H, F, or C.sub.1 -C.sub.4 alkyl. PA1 (1) when R.sub.1 is Cl, then L is Cl or Br and R.sub.2 is H; PA1 (2) when L is NR.sub.3 R.sub.4 or N.sup.+ R.sub.3 R.sub.4 R.sub.4 ', then R.sub.3 or R.sub.4 can not be H; and PA1 (3) when R.sub.3 is OCH.sub.3, then R.sub.4 is CH.sub.3. PA1 (1) when R.sub.1 is Cl, then L is Cl or Br and R.sub.2 is H; PA1 (2) when L is NR.sub.3 R.sub.4 or N.sup.+ R.sub.3 R.sub.4 R.sub.4 ', then R.sub.3 and R.sub.4 cannot be H; and PA1 (3) when R.sub.3 is OCH.sub.3, then R.sub.4 is CH.sub.3. PA1 L is as defined for Formula II; PA1 Z is CH or N; and PA1 R.sub.9 is C.sub.1 -C.sub.3 alkyl.
Compounds of Formula (ii), and their use as antidiabetic agents, are reported in J. Drug Res. 6, 123 (1974). ##STR2## wherein R is pyridyl.
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food needs, such as soybeans, corn, wheat, and the like. The current population explosion and concomitant world food shortage demand improvements in the efficiency of producing these crops. Preventing or minimizing the loss of a portion of such valuable crops by killing or inhibiting the growth of undesired vegetation is one way of improving this efficiency.
A wide variety of materials useful for killing or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. The need still exists, however, for more effective herbicides that destroy or retard weeds without causing significant damage to useful crops.
In U.S. Pat. No. 4,127,405 compounds of the following formula are taught: ##STR3## wherein R.sub.1 is ##STR4## R.sub.3 and R.sub.6 are independently hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, nitro, trifluoromethyl, cyano, CH.sub.3 S(O).sub.n -- or CH.sub.3 CH.sub.2 S(O).sub.n --;
or their agriculturally suitable salts; provided that: